Formamidine acetate → HCID 135682057, compound

HRID 1791202Notes

Reaction equation

HRID 1791202 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:20])([F:19])[F:18])=[CH:7][C:6]=1[NH2:21])=O.C(O)(=O)C.[CH:26](N)=[NH:27]>COCCO.[OH-].[Na+]>[F:18][C:17]([F:20])([F:19])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:8]1[CH:7]=[C:6]2[C:5]([C:3](=[O:2])[NH:27][CH:26]=[N:21]2)=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 160693Formamidine acetateHCID 59015784HCID 59015784, compound

Product 1

HCID 135682057HCID 135682057, compound

Reagents, catalysts & solvents 2

HCID 80192-MethoxyethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Heat a solution of 3-amino-2′-trifluoromethyl-biphenyl-4-carboxylic acid methyl ester (5.0 g, 0.0169 mol) and formamidine acetate (2.8 g, 0.0203 mol) in 2-methoxyethanol at reflux for 8 hours. Cool the mixture and concentrate under reduced pressure to give a dark oil. Dissolve the residue in 10% NaOH and wash the aqueous with ether (3X). Bring the aqueous layer to pH ˜4 using 12N HCl to produce a milky solution. Extract the solution with EtOAc, wash the EtOAc with brine, dry (Na2SO4) and concentrate under reduced pressure to give 7-(2-Trifluoromethyl-phenyl)-3H-quinazolin-4-one as a beige solid.

Workup

  1. temperatureat reflux for 8 hours
  2. temperatureCool the mixture
  3. concentrationconcentrate under reduced pressure
  4. customto give a dark oil
  5. washwash the aqueous with ether (3X)
  6. customto produce a milky solution
  7. extractionExtract the solution with EtOAc
  8. washwash the EtOAc with brine
  9. dry with materialdry (Na2SO4)
  10. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-55ccd850a1ba47d9acc11261c2133a02
Source dataset
uspto-grants-2006_07
Patent number
US07074799B2

Reaction notes

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